Benjamin Whipple was born September 16, 1755 in Hardwick, Worcester County, Massachusetts. He was the fifth of nine children of Benjamin (1727-1806) and Hepzebah (Crosby) Whipple (1727-1797). Benjamin moved with his parents to Bennington, Bennington County, Vermont in 1761.

Benjamin was in the battle of Bennington on August 16, 1777 while serving in Captain Samuel Robinson's (Bennington) Company of Vermont Militia. Two days later, on August 18th, he enlisted into Captain John Warner's Company of Green Mountain Rangers and served until December 3, 1777, when he was mustered out.

During the remainder of the Revolutionary War, Benjamin served at different times in cases of emergency and alarm. In the first part of November 1778, he served 7 days in Captain Simeon Wright's (Rutland) Company in Col. Gideon Warren's (Fifth) Regiment of Vermont Militia. In the later part of May 1779, he served 9 days in Captain Samuel Robinson's (Bennington) Company, 2nd Regiment of Vermont Militia when that Company went east over the mountains to assist the Cumberland County (now Windham County, Vermont) Sheriff in the execution of his Office. During the latter part of March 1780, he served 3 days in Captain Simeon Wright's (Rutland) Company in Col. Gideon Warren's (Fifth) Regiment of Militia for a scout to the Lake against Crown Point and then to Ticonderoga. In early August 1780, he served 8 days in Captain John Spafford's Company raised from Colonel Ebenezer Allen's 5th Regiment of Vermont Militia for duty at Pittsford, Rutland County, Vermont. Between October 12th and November 12th 1780, he served 15 days in Captain Nathaniel Blanchard's (Rutland) Company, Colonel Ebenezer Allen's 5th Regiment of Vermont Militia, for an alarm caused by the British Raid lead by Major Christopher Carleton upon Fort Ann in Charlotte (now Washington) County, New York and Fort George at the southern end of Lake George (now in Warren County), New York. Beginning on October 21, 1781, he served 10 days as a Drummer in Captain Nathaniel Blanchard's (Rutland) Company, Colonel Thomas. Lee's 5th Regiment of Vermont Militia for duty at Castleton, Rutland County, Vermont.

Benjamin married Silence Bundy (1761-1805) on October 15, 1779 possibly at Rutland, Rutland County, Vermont. They had 12 children, 5 sons and 7 daughters: Ithamar born 1780, Joel born 1782, Benjamin (1784-1803), Elizabeth born 1786, Sally born 1787, David born 1791, Jonathan born 1793 or 1794, Lydia born 1796, a daughter born 1798 who lived but 12 days, Nathan born 1800, Hepzebah born 1802, and Benjamin born 1805. Silence, Benjamin's 1st wife, died in what is now Ledyard, Cayuga County, New York two months after the birth of her twelfth child, on March 8, 1805.
In 1794, Benjamin moved with his family from Rutland, Rutland County, Vermont to what is now Venice, Cayuga County, New York and later to what is now Ledyard in the same county. The towns of Venice and Ledyard were both taken from the town of Scipio, Cayuga County, New York in 1823.

In Venice, Benjamin became a prominent figure in the Baptist Church upon becoming licensed to preach. Here he served as a deacon and, although not ordained, as the church's 2nd Pastor.

In 1806, Benjamin moved to Groton, Tompkins County, New York where he assisted in the organization of the First Baptist Church of Groton. In the same year, he married his 2nd wife Sally Luther - age 31. In 1807, Benjamin was ordained in Groton. He continued to serve the Groton church and others nearby for several years until 1812.

In he spring of 1812, Benjamin moved to Sennett Corners, Sennett, Cayuga County, New York when he became Pastor of the Baptist Church located there. He resided in Sennett and served as Pastor of the church until his death on March 8, 1813. He is buried in the Sennett Rural Cemetery (the old part of the Baptist cemetery south of Sennett Corners).